Potassium Phosphate, Tribasic → 2-Phenylisonicotinic acid

Temperature

150 °C

Preparation H1, Step 1: A mixture of 2-bromo-4-pyridinecarboxylic acid (1.1 g, 5.45 mmol), phenylboronic acid (1.3 g, 10.9 mmol), 2.0 M potassium phosphate (aq) (8.2 mL, 16.34 mmol), and DMF (10 mL) in a 20 mL microwave tube was degassed under vacuum/Ar. A catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added to the tube, the mixture was degassed again, the tube was sealed, and the reaction was heated at 150° C. in the microwave for 30 min. The reaction mixture was filtered, the filtrate was concentrated in-vacuo, and the residue was dissolved in water (10 mL). The mixture was acidified to pH=6 with the addition of 1.0 N HCl, and the resulting precipitate was collected by filtration, rinsed with two portions of ice-cold water, and air dried to yield 575 mg of 2-phenylisonicotinic acid as an off-white solid. MS (ES+)=200 (M+H+).

1. customPreparation H1, Step 1
2. customwas degassed under vacuum/Ar
3. additionA catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added to the tube
4. customthe mixture was degassed again
5. customthe tube was sealed
6. filtrationThe reaction mixture was filtered
7. concentrationthe filtrate was concentrated in-vacuo
8. dissolutionthe residue was dissolved in water (10 mL)
9. additionThe mixture was acidified to pH=6 with the addition of 1.0 N HCl
10. filtrationthe resulting precipitate was collected by filtration
11. washrinsed with two portions of ice-cold water, and air
12. customdried

ORD record

ord-ca6694a26aad44ba88a0c3c9a3f4e721

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07378409B2